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(4R)-Ethyl 4-(4-chlorophenyl)-2-hydroxy-5-oxo-2,3,4,5-tetrahydropyrano[3,2-c]chromene-2-carboxylate
The title compound, C(21)H(17)ClO(6), is optically pure and adopts an R configuration. It was obtained by an organocatalytic asymmetric Michael addition of 4-hydroxycoumarin with (E)-ethyl 4-(4-chlorophenyl)-2-oxobut-3-enoate. The structure consists of a tetrahydropyran unit fused to the coumar...
Autores principales: | , , , |
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Formato: | Texto |
Lenguaje: | English |
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International Union of Crystallography
2009
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2980058/ https://www.ncbi.nlm.nih.gov/pubmed/21580101 http://dx.doi.org/10.1107/S1600536809051976 |
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author | Wang, Yifeng Zhang, Wei Xu, Xiangsheng Zhang, Guangcun |
author_facet | Wang, Yifeng Zhang, Wei Xu, Xiangsheng Zhang, Guangcun |
author_sort | Wang, Yifeng |
collection | PubMed |
description | The title compound, C(21)H(17)ClO(6), is optically pure and adopts an R configuration. It was obtained by an organocatalytic asymmetric Michael addition of 4-hydroxycoumarin with (E)-ethyl 4-(4-chlorophenyl)-2-oxobut-3-enoate. The structure consists of a tetrahydropyran unit fused to the coumarin ring ring system. The hydroxyl and phenyl groups are on the same side of the tetrahydropyrane ring. The benzene ring is almost perpendicular to the coumarin ring [dihedral angle of 72.89 (3)°]. In the crystal structure, intermolecular O—H⋯O hydrogen bonds are observed. An intramolecular O—H⋯O contact also occurs. |
format | Text |
id | pubmed-2980058 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2009 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-29800582010-12-30 (4R)-Ethyl 4-(4-chlorophenyl)-2-hydroxy-5-oxo-2,3,4,5-tetrahydropyrano[3,2-c]chromene-2-carboxylate Wang, Yifeng Zhang, Wei Xu, Xiangsheng Zhang, Guangcun Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(21)H(17)ClO(6), is optically pure and adopts an R configuration. It was obtained by an organocatalytic asymmetric Michael addition of 4-hydroxycoumarin with (E)-ethyl 4-(4-chlorophenyl)-2-oxobut-3-enoate. The structure consists of a tetrahydropyran unit fused to the coumarin ring ring system. The hydroxyl and phenyl groups are on the same side of the tetrahydropyrane ring. The benzene ring is almost perpendicular to the coumarin ring [dihedral angle of 72.89 (3)°]. In the crystal structure, intermolecular O—H⋯O hydrogen bonds are observed. An intramolecular O—H⋯O contact also occurs. International Union of Crystallography 2009-12-19 /pmc/articles/PMC2980058/ /pubmed/21580101 http://dx.doi.org/10.1107/S1600536809051976 Text en © Wang et al. 2010 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited. |
spellingShingle | Organic Papers Wang, Yifeng Zhang, Wei Xu, Xiangsheng Zhang, Guangcun (4R)-Ethyl 4-(4-chlorophenyl)-2-hydroxy-5-oxo-2,3,4,5-tetrahydropyrano[3,2-c]chromene-2-carboxylate |
title | (4R)-Ethyl 4-(4-chlorophenyl)-2-hydroxy-5-oxo-2,3,4,5-tetrahydropyrano[3,2-c]chromene-2-carboxylate |
title_full | (4R)-Ethyl 4-(4-chlorophenyl)-2-hydroxy-5-oxo-2,3,4,5-tetrahydropyrano[3,2-c]chromene-2-carboxylate |
title_fullStr | (4R)-Ethyl 4-(4-chlorophenyl)-2-hydroxy-5-oxo-2,3,4,5-tetrahydropyrano[3,2-c]chromene-2-carboxylate |
title_full_unstemmed | (4R)-Ethyl 4-(4-chlorophenyl)-2-hydroxy-5-oxo-2,3,4,5-tetrahydropyrano[3,2-c]chromene-2-carboxylate |
title_short | (4R)-Ethyl 4-(4-chlorophenyl)-2-hydroxy-5-oxo-2,3,4,5-tetrahydropyrano[3,2-c]chromene-2-carboxylate |
title_sort | (4r)-ethyl 4-(4-chlorophenyl)-2-hydroxy-5-oxo-2,3,4,5-tetrahydropyrano[3,2-c]chromene-2-carboxylate |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2980058/ https://www.ncbi.nlm.nih.gov/pubmed/21580101 http://dx.doi.org/10.1107/S1600536809051976 |
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